Acetic Anhydride → 3-[1-(Acetamido)tridecyl]-5-trimethylsilylfuran

HRID 1534340Notes

Reaction equation

HRID 1534340 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH:9]([C:22]1[CH:26]=[C:25]([Si:27]([CH3:30])([CH3:29])[CH3:28])[O:24][CH:23]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(N(CC)CC)C>ClCCl>[C:1]([NH:8][CH:9]([C:22]1[CH:26]=[C:25]([Si:27]([CH3:30])([CH3:29])[CH3:28])[O:24][CH:23]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 150370773-(1-Aminotridecyl)-5-trimethylsilylfuran

Product 1

HCID 150370783-[1-(Acetamido)tridecyl]-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.1 ml) was added to a solution of 3-(1-aminotridecyl)-5-trimethylsilylfuran (89.8 mg, 0.27 mmol) and triethylamine (0.1 ml) in dichloromethane (1 ml) at room temperature. Stirring was continued overnight (14 hours) while the cooling bath attained room temperature. The residue, after solvent removal, was purified by preparative TLC (20×20 cm, 1000μ; developed with 60% ethyl ether/hexane). The title amide was obtained as a pale yellow oil.

Workup

  1. custom(14 hours)
  2. customwhile the cooling bath attained room temperature
  3. customThe residue, after solvent removal
  4. customwas purified by preparative TLC (20×20 cm, 1000μ; developed with 60% ethyl ether/hexane)

Sources & evidence

ORD record
ord-18e37563963d4170a4442945e62febe9
Source dataset
uspto-grants-1992_02
Patent number
US05089485

Reaction notes

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